I'm a long-time Winamp user but I have yet to try ml ipod. I have a few questions that I can't seem to find documented answers too:

1) can ml ipod index & load files into the Apple DB using longer folder and file names than the 4-char ones iTunes uses? Can it keep files from the same album in one dir (again unlike iTunes)?

2) what codecs can ml ipod load without needing to transcode for Apple OS playback?

Some background (I hope this is understandable):

I use the Rockbox OS on an 80GB iPod Video (5.5 Gen). Rockbox is great as it lets me manage my audio files w/o needing a DB and has many codec plugins. It does have one drawback though: it isn'tsupported by many iPod accessories, like the Bose care stereo in our 2010 Nissan Altima. Because of the Bose unit can understand iPods but is severely limited in dealing with generic USB devices, I want to populate the iPod DB and let it recognize the device as an "Apple iPod". the device can "dual boot" RB or Apple.

Rockbox has it's own tag DB but it's not mandatory to use it as it is to play files from the Apple OS and one can simply play files from any dir. Unfortunately, RB can't use the Apple DB and the Apple OS requires it's own DB and file structure, including 4-char file names and files randomly distributed over it's cryptic file structure.

I already have files loaded in my own tree structure for RB. I don't want to use iTunes and hope to not duplicate audio files. So, to be able to play the same audio file from both RB and Apple OS, the files must be limited to the Apple codecs (mp3, Mp4, and uncompressed?) and I will need also to use the RB Tag DB. Basically I want to index the same set of files in both the Apple and RB DBs. I realize I won't be able to have all files available in RB also available in Apple OS without transcoding and duplicating, but that's ok.

1) yes, but......
There's an option to have ml ipod use descriptive path and file names HOWEVER as warned, the iPod can't play the file. This may be a perfect solution for me IF the Bose unit can follow the path correctly when in iPod mode.